Satisfied
by bookworm7117
Summary: Series of one-shots based on the song "Satisfied" from Hamilton the musical. Different universe, points of views, and pairings.


CHUCK

Chuck looked around the room. A bright beautiful bouquet of peonies on each table. Smiling faces waiting expectantly. Then he saw her: Blair Waldorf. A vision in white. She looked every bit the princess she always dreamt of being. She beamed at him, and he smirked at her. Then his best friend, Nathaniel Archibald, kissed the bride on the cheek. He grinned his casual grin at Chuck, who nodded at him.

The DJ announced, "Alright! Alright! That's what I'm talking about! Now everyone give it up for the best man: Chuck Bass!"

Chuck stood giving a small smile. He raised his glass. "A toast to the groom!"

Everyone in the room cheered and drank, "To the groom!"

"To the bride!"

Everyone in the room cheered and drank, "To the bride!"

Blair laughed taking a drink, "Leave it to Bass to figure a way to get us all a little more drunk."

Chuck shrugged at her, grinning, "From your best friend who is always by your side."

"Nate has come a long way from that boy at St. Jude's who just wanted to skip class and light one up."

Blair shot him a deadly look, and Nate just laughed good-naturedly.

"And that has a lot to do with the dazzling young woman next to him," Chuck's eyes bore into Blair's own. She seemed pleased, a slight pink rising to her cheeks.

"Blair was always the Queen of Constance and Nate was rightfully her Prince Charming. So tonight I'd like to toast to their union - and the hope that it provides to the rest of us, even me, the notorious bachelor of Manhattan," Chuck paused, letting the laughter subside. It was a bit painful being the brunt of the joke - Chuck Bass in a relationship, in love, what a joke. If they only knew...

"Being around a love like theirs," Chuck gestured between the two, "makes you think it might be possible for you too."

Blair found his eyes. Hers held a question. Nate was smiling like an idiot beside. He had no clue.

"So to Nate and Blair, may you always be _satisfied_!"

Blair sat up straighter at the last line. Everyone else drank and cheered. Nate patted Chuck on the back, then gave him a big hug. Over Nate's shoulder, Chuck caught Blair's eye as she sipped her dom. She glared at him.

Chuck obviously remembered the reference, and he knew Blair would too.

* * *

Chuck could recall that night like it was yesterday. He thought he might regret it for the rest of his days. He remembered the party girls and socialites tripping over themselves to win Chuck Bass's praise. They dragged their nails down his suit jacket. They tried to kiss him. He pushed them all off when he saw her. The gala was lowlight, almost candlelight. She looked like a dark angel. Chuck knew he would never forget the first time he saw her face.

Brown locks cascaded down her shoulders. Big brown, intelligent eyes found his own. She wore a black dress with a tight bodice and a flair skirt. Her lips were bright red. She worked her way around the floor, conversing with everyone in a delightful manor. He saw her mother reprimand her, but the girl composed herself quickly. She was back to being bubbly and striking up intelligent conversation with businessmen around the room. Her style was killer. She was the epitome of the Upper East Side, and yet, Chuck could tell she didn't quite fit in. She wasn't like everyone else. She didn't just settle for the life she had. There was an eagerness, a devotion, an ambition about her that Chuck admired - everything she got, he thought she probably worked for. She didn't hold herslef like someone who relied on their trustfund and mom and dad's contacts. She exuded real authority, real power. He admired her for it. Chuck sauntered up to her with a smirk.

She met his smirk with her own, and her voice dripped with placation, "Hi."

Chuck sucked in a breath. He forgot his name for a moment, lost in her eyes. His heart was beating faster than it ever had. His face flushed. Every part of his body felt like it was on fire. Her eyes scorched into his brain. This wasn't like the other times he had approached the most beautiful girl in the room. Those times it had been a game. He had been focused on conquering new territory. But it was different this time - it wasn't a game. He _felt_ something more than boredom and mild interest.

Blair continued, giving him a look, "Cat got your tongue."

"Would you like to dance?" Chuck panicked, but figured that usually that's what one would ask at a gala. He wouldn't know because he normally just approached a girl and asked her if she wanted to see the roof or get out of here. If they were more difficult, he'd just say what he needed to to get them to leave with him. It was easy. This time, though, it's like his entire playbook went out the window.

Blair rolled her eyes and took his hand. He led her to the dance floor. His hand carefully gripping her hand. The other squeezed her waist tightly and drew her closer to him. Her breath caught. He smirked. She noticed and her eyes narrowed, ready to strike back.

Blair stood on her tiptoes until her breath tickled the skin below his ear, "You strike me as a man who has never been satisfied."

Chuck laughed in shock. She was feisty. He reveled in it. Then he gasped, drawing back to look at her, in mock shock, "I'm sure I don't know what you mean." He honestly couldn't decipher if she knew who he was and was playing to it, or if her words had an entirely different, and more appropriate, meaning.

She laughed freely.

"You forget yourself," he reprimanded, but he was smirking. A fire alight in his eyes.

"You're like me. I'm never satisfied," Blair explained, her eyes gleaming.

He raised an eyebrow, "Is that right? Do you know who I am? I'm Chuck Bass: I'm sure you're aware of my _reputation_. I assure you I have been thoroughly _satisfied_."

Blair laughed, a real, genuine laugh. She hadn't meant it that way, but she was even more intrigued with him after discovering his mind could wander to darker places. Although she rarely showed that part of herself to anyone. It wasn't ladylike. "Blair Waldorf."

Chuck grinned, "Pleasure to meet you. If you truly haven't ever been _satisfied_ , I would love to oblige..."

She rolled her eyes, "I meant that there are a million things I haven't done yet-"

"Aren't there always?" Chuck smiled wistfully not fully comprehending her point.

"Well, sure. But just you wait, I'm going to actually _accomplish_ mine."

He smiled down at her, "I don't doubt it."

She beamed up at him with a pleased smile. "Haven't you got big plans, Bass?"

He liked the familiarity with which she said his last name, "Probably not as big as yours, Waldorf."

She laughed happily. He spun her around. He loved dancing with her. Chuck wanted this moment to last forever. He had never felt like this before; he'd never felt equal to someone and yet so entirely beneath someone.

"So _Waldorf_ ," Chuck continued. "a prestigious name befitting a woman of your caliber."

Blair smiled, "Yes, we Waldorfs come from a long line of respectable women. But that's rather unimportant."

The conversation lasted maybe two minutes, maybe three minutes. Chuck had never met someone who could spar words with him like this girl. She was brilliant and witty. He enjoyed every second of their conversation, and he knew that he was right. They both wanted more out of this life. They both had big plans. They would never be satisfied with living off their trustfund. They had parents to make proud, and their own ambitions to please.

Chuck always thought he would probably end up alone. He would date around like his father. Searching, always searching, for more and never finding it. But here she was. Someone who he could see himself being with, changing for. What was the catch? It felt like a dream. She was even flirting with him. A girl of that status was not repelled by him and his reputation immediately. A feat for sure.

And she was the most gorgeous woman Chuck had ever seen. Her ivory skin complimenting her red lips. Her big brown eyes drawing him into a dreamlike state. Everything about her was intoxicating down to her Chanel No.5 perfume.

The song ended. They paused a moment, thinking about what happened next. Another dance?

Then over her shoulder, Chuck caught Nate's eye. And he remembered: Nate had told him he was supposed to meet a girl named Blair here. His grandfather had selected a list of suitable girls for his grandson, and Blair had been the only one Nate was interested in. He was infatuated with her. Chuck kicked himself for not recalling the name immediately. He sighed. Nate had already told him that Blair was "his." Chuck wasn't to mess with Nate's wife-material just for the sex. That's what Nate would think if he saw Chuck trying to woo Blair. Nate's eyes searched the gala helplessly. He was smitten with the girl. He had only chatted online with her a couple times.

Chuck realized three fundamental things at the exact same time.

So he took Blair's hand again and led her toward her real Prince Charming.

"Where are you taking me?"

He turned back to her with a smirk, "I'm about to change your life."

She giggled, "Then by all means, lead the way."

Chuck realized that he's a boy in a world in which his only job is to eventually run Bass Industries successfully. His father has no other sons. He's the only one. He has to social climb, fight, and earn billions. He doesn't have time for love and romancing; his father certainly didn't. They were new money, and people on the Upper East Side only tolerated such people if they were richer than them. Chuck had a terrible reputation along with being from new money, and the gossip in New York City is insidious. There was no way that Blair would ever consider Chuck a real option. Maybe for a night or a fling to piss off her uptight mother, but Blair would never marry Chuck Bass. She was a Waldorf. Let alone would his father ever condone marrying a girl like Blair, especially for the sake of love. His father believed sacrifice was necessary to the success of the company; he also believed that love was a wretched curse. Chuck couldn't quite blame him as his beloved wife had died giving birth to his disappointment of a son. Blair could only ever be a business deal to Chuck, and Blair deserved more than that. She deserved a Prince Charming, but that didn't mean that Chuck wanted her any less.

Chuck lead Blair up to Nate who grinned one his big smiles. His shaggy hair giving him a carefree playboy look, but his preppy style asserting his Golden Boy status.

"Nathaniel Archibald. It's a pleasure to meet you," he held out a hand to Blair who took it with surprised eyes.

"Archibald?" Blair commented with recognition, but looked questioningly at Chuck.

"My best friend."

Chuck also realized that Blair was after Nate because he was an Archibald. After all, she had been chatting with Nate online after, probably, some kind of arrangement between Nate's grandfather and Blair's mother. Neither of the two teens seemed to mind, however, and Chuck realized that an Archibald, a Van Der Bilt, would elevate Blair's status. As a respectable Waldorf, marrying a Van Der Bilt would put her in the perfect position to become a political force. The only reason she was talking to Chuck was because she didn't know who he was or because of his money. He has nothing else to offer - he doesn't have the kinds of connections that the Van Der Bilts do. Chuck knew his reputation would instantly taint hers. She wouldn't be able to achieve all her goals of ruling elitist societies and dominating the world. And he knew that he'd be naive to set that aside. That's why Chuck went ahead and introduced her to Nathaniel. He had already promised his best friend he'd do that much at least.

Now Blair was his bride. _Nice going, Chuck,_ he thought. _She was right, you will never be satisfied._

"It's so great to finally meet you. I love chatting with you. Thank you for putting up with my grandfather's weirdness about the whole thing."

Blair laughed, a sound that made Chuck's heart soar and also turn to stone as he was not the one making her laugh anymore, "If it takes a dozen awkward exchanges with your grandfather for us to meet, it will have been worth it."

Chuck smiled sadly, "I'll leave you to it."

Blair turned to him as if she was going to say something, but shook that notion out of her mind. His eyes fell to the floor. He shuffled away.

Chuck knew that he'd done the right thing. He knew Nate like he knew his own mind. There was no one as trusting or as kind as his best friend. If he told Nate how he felt about Blair, his best friend would be be silently resigned. Blair would be his. Nate would say he was fine, but he would be lying. Chuck could see the sparkle in his eyes. He was helpless, stunned and enthralled with Blair's beauty and intellect. Chuck could not blame him. They hadn't met a girl as striking as her in all their years.

* * *

Chuck blinked. He was back in the present, out of his own head, his own memories and regrets. He smiled at the happy couple. He may have taken himself out of the equation, but when he fantasized at night, he couldn't help that his mind wandered to Blair. Her eyes, big, brown, beautiful always struck his mind. He would lay in bed at night thinking about what could have been, wishing for that other life, but knowing it could never exist except in the dark, quiet hours alone in his bed. Chuck wondered and regretted and wished and hoped. His mind was full of "what if"s and "if only"s. He wondered what would have been if he hadn't sized Blair up so quickly. If he hadn't dismissed her obvious flirtation for nothing more than a little rebellion. If he hadn't underestimated her ability to choose him, to choose someone who would likely overturn all her plans and goals and dreams and expectations. Would she have picked him if he had given her the chance?

Chuck would never know, but at least she was his best friend's wife. Nate deserved a woman like Blair. Nate was the best person he knew. Upstanding, brilliant, loyal, and true. Chuck knew he wasn't just happy for his best friend's happy marriage; he enjoyed having Blair around often. Her eyes, intelligent and fierce, stayed in his life forever. She was always within reach, but still untouchable, off-limits. It was the cruelest form of torture, but Chuck reveled in it. He would never get over her, he knew. He would never find love, but his father made sure he knew from a young age that he was not entitled to love.

At the end of the night, the happy couple said their goodbyes. They held hands going down an aisle as everyone popped streamers above their heads. Nate hugged Chuck, grinning widely, happy for his best friend who was more like a brother.

"I'm finally gonna follow your advice and seal the deal," Nate laughed good-humoredly. It was a harmless joke. Blair was his wife. Chuck blanched at the thought of the two of them together, but just chuckled at Nathaniel's lack of experience.

Then Blair hugged him. The hug lasted for what seemed like forever. He tried to convey all his feelings into a hug, but what was the point really? It was just another hug on her wedding day, her wedding day where she had just married his best friend. But Chuck reveled in holding her close not knowing when he would get another chance. He could smell her Chanel No.5 perfume. It invaded his senses.

She pulled back, but stared him straight in his eyes.

Chuck fumbled for words to say. She waited, expectantly, as if knowing he had something to say.

"I know that Nate will be happy as your husband."

Blair nodded a small smile appearing that didn't touch her eyes. He wondered why the light in her eyes seemed darker rather than light and airy as it had before during the ceremony. .

"And me?" she asked, barely a whisper. He could see the fear, the enticement in her eyes. She was flirting with him. She was devastated. She was hopeful. He couldn't decide what emotion her eyes were declaring.

Chuck told the truth with a smirk, "You will never be satisfied."

She gave a small smirk, "Neither will you, Bass."

She gave him a light peck on the cheek and sauntered back to the main aisle. She found Nate's hand and giggled. Then they drifted down the aisle toward the limo waiting for them. They both gave one last wave grinning huge smiles, and then they were gone.

Chuck was left standing there speechless, still feeling her lips on his cheek and hearing her words ringing in his ears.

He knew it, too. He would never be satisfied because who he truly wanted was already taken and he would never put his own happiness above his best friend Nate's, especially when he wasn't sure he could even make Blair happy. Who could make her happy? She had said it herself. She would never be satisfied. It had been a challenge and a truth. He had given her what he thought she wanted - the perfect life with Nate. And now, she was going to torture him with secret smiles, private exchanges, and pecks on the cheek.


End file.
